Azodyestuffs and process of making the same



Patented Jan. 6, 1925.

UNITED STATES PATENT OFFICE.

N WAGNER, OF HOOHS T-ON-THE-HAIN, AND OTTO SOHS'I, OF HANAUON-THE- IAIN,GERMANY, ASSIGNORS T FARBWERKE VORM. MEISTEB LUCIUS & BRUN- mo, OFHOGHST-ON-THE-IAIN, GERMANY, A CORPORATION OF GERMANY.

AZODYESTUFFS AND PROCESS OF MAKING THE SAME.

4 I0 Drawing.

To all whom it may concern Be it known that we, HERMANN WAGNER and O'rroSons'r, citizens of Germany, residin at. Hochst-on-the-Main, Germany, 5and anau-on-the-Main, Germany, have ina. vented certain new and usefulIm rovements in Azodyestufi's and Processes of aking the Same, of whichthe following is a specification.

We have found that dyestufi's or dyein s of excellent fastness areproduced by coup ing the diazo-com ounds obtained from the alkyl-,arylan aralkylamides of the alkyloxy-3-ammo-1-benzoic acids with any ar1- amides of the 2.3-hydroxynaphthoic acid.

B this process there are obtained dyestufl's 0 an excellent clear redtint with a blue hue possessing the important property of beingutilizable for the production of fast aliza0 arine-pink-shades.

Examples.

in which X stands for any acid residue.

4. The material is padded with a solution of:

24,9 g. of 2.3-hydroxynaphthoic acid 4- 75 chloro-2-anisidide [SNH.OCH,.C1=1 2 5), 80 ccm. of caustic so a solution 22 B., g.

Application filed December 26, 1923. Serial No. 882,819.

soda solution 34* B., 3 ccm. of sodium Turkey red oil 50%, 50 com. ofhot water are made up to 1 litre with cold water. The impregnated yarnis wound oil and dyed in the following diazo solution.

1,6 g. of 3amino-4-methoxy-l-benzoic acid anilide are (pasted with 1,7ccm. of hydrochloric aci 22 B. and 25 ccm. of water, cooled b additionof 25 com. of ice and mixed whi e stirring with a solution of 0,5 ccm.of sodium nitrite in 10 ccm. of water. The whole is made up with coldwater to 1 litre and before use mixed with 1,34 of sodium acetate.

A ter dyeing the material is well washed and soaped.

3. The material is padded with a solution of: 21,1 g. of2.3-hydroxynaphthoic acid o-toluidide (CH,:NH,=1:2), 60 com. of

caustic soda solution 22 B., 20 g. of Para soap PN. made u to 1 litre.

Then there is ried and printed with the following colour:

24,2 of 3-amino-4-methox -1-benzoic acid ani ide are well pasted wit 140com. of water and 24 ccm. of hydrochloric acid 22 Be, cooled with 150 g.of ice and there are added 8 g. of sodium nitrite dissolved in com. ofwater, the whole is stirred into 524 g. of tragacanth 1000, there arethen added 60 g. of aluminium sulphate 1: 1 dissolved in water and,before use, 20 g. of sodium phosphate, ca.

The reactlon involved in the foregoing examples 1, 2 and 3 is asfollows:

OOH:

of Para soap PN, made up to 1 litre, then printed with the printingcolour mentioned in example 2.

The reaction involved in this example is similar to that of examples 1,2 and 3, the formula of the 2.3-hydroxynaphthoic acid-4-chloro-2-anisidide acid involved being:

(Ii ai OCH:

Diaeo-solution.

2,42 of 3-amino-4-methoxy-l-benzoic acid anilide are dissolved in 200com. of warm water and 2,4 ccm. of hydrochloric acid 22 B. cooled with600 com. of cold water and 100 g. of ice, then there are added 0,8 g. ofsodium nitrite dissolved in 16 com. of water, and before use there areadded 2 g. of sodium acetate, the whole is made up to 1 litre and, asabove indicated, stirred into 3 12 g. of 2.3-hydroxynaphthoic acid 5-chloro 2 toluidide (NH.OH,.C1:1 2 4 10,5 com. of caustic soda solution22 B., 136 g. of sulphate of barium made up to 1 litre.

The sodium salt of the 2.3-hydroxynaphthoic acid-5-chloro-2-toluidide ofthe foregoing example has the formula:

(so 4H9 6. The am is impregnated with the following so ution:

1,25 g. of h droxynaphthoic acid-4-chloro- 2-anisididc H.OCH,.C1=1:2:5), 2,? com.

of caustic soda solution 34 B., 3 com. of'

sodium Turkey red oil 50 com. of hot water, with cold water made up to 1litre.

The impregnated yarn is wound off and dyed with the followingdiazo-solution:

1,6 g. of 3-amino-4-methoxy-l-benzoic acid anilide are pasted with 1,7ccm. of hydrochloric acid 22 B. and 25 com. of water, then cooled byaddition of 25 com. of ice and mixed while stirring with a solution of0,5 g. of sodium nitrite in 10 com. of water and with cold water made upto 1 litre, before use there are added 1,34 g. of sodium acetate.

After dyeing it is washed and soaped.

A clear pink with a blue hue is obtained.

If the 3-amino-4-methoxy-1-benzonic acid anilide; used in Ex. 6 isreplaced by an equivalent quantity of 3-amino-4-ethoxy-1- benzoic acidanilide or of the 3-amino-4- methoxy-l-benzoic acid-2-toluidide, thereare produced very similar pink shades, whereas y usin3-amino-4-methoxy-1-benzoic acid ethylani ide there is obtained a pinkwith .a somewhat yellower hue. Pink shades all of a somewhat yellowerhue, are roduced, if the 2.3-hydroxynaphthoic aci -4-chloro-2-anisidide, mentioned in example 6 is replaced by an equivalent quantityof 2.3-hydroxynaphthoic acid-5-chloro-2-toluidide, ((1H,:NH Cl:1:2:5)and if the latter is coupled with the aforesaid diazo-compounds.

. The 3-amino-4-ethoxy-1-benzoic-acid-ani lide,3-amino--methoxy-l-benzoic acid-2- toluidide and3-aminol-methoxy-l-benzoic aciril ethylanilide referred to have theformu 8e By alkyloxy-3-amino-1-benzoic acids we mean not only the parentcompounds but also their homologues and substitution products.

Having now described our inventlon, what we claim is:

1. As new products the dyestuifs obtainable by coupling the diazocompounds of alkyl-aryl-and aralkyl amides of thealkyloxy-3-amino-1-benzoic acids with any 2.3-hydroxynaphthoic acidarylides which, on reduction eld an aromatic amino and an arylide of t e1-amino-2-hydroXy-3-naphthoic-acid.

2. Process for preparing azo-dyestufis which consists in coupling thediazo compounds of alkylaryland aralkylamides of thealkyloxy-3-amino-1-benzoic acids with any 2.3-hydroxynaphthoic acidarylamides.

In testimony whereof, we aflix our signa- 0 tures.

HERMANN WAGNER. O'ITO SOHST.

2.3-hydroxynaphthoic acid arylides which, In testimony whereof, we afiixour signa- 10 on reduction 1eld an aromatic amine and an tures.

aryllde of t e 1-amino-2-hydro1iy-3-naphtholc-acid. HERMANN WAGNER. 5Process for preparing azo-dyestufls OTTO SOHST.

which consists in coupling the diazo compounds of alkylarylandaralkylamides of Witdxessesz the alkyloxy-3-amino-1-benzoic acids withG. C. L. B. WYnns, any 2.3-hydroxynaphthoic acid arylamides. JANESmnsrr.

Certificate of Correction.

It is hereby certified that in Letters Patent No. 1,522,089, grantedJanuary 6, 1925, upon the application of Hermann Wagner, ofHochst-on-the-Main, and Otto Sohst, of Hanau-on-the-Main, Germany, foran improvement in Azodyestufls and Processes of Making the Same, errorsappear in the printed specification requiring correction as follows:Page 1, line 68, after ca. insert 1 kg; page 2, line 63, for themisspelled word ben zonic read benzoic; same page, line 93, followingthe formulae, insert the word respectively; and that the said LettersPatent should be read with these corrections therein that the same mayconform to the record of the case in the Patent Oifice.

Signed and sealed this 10th day of March, A. D. 1925.

[HEAL] KARL FENNING,

Acting Commissioner of Patents.

Certificate of Correction.

It is hereby certified that in Letters Patent No. 1,522,089, grantedJanuary 6, 1925, upon the application of Hermann Wagner, ofHochst-on-the-Main, and Otto Sohst, of Hanau-on-the-Main, Germany, foran improvement in Azodyestuifs and Processes of Making the Same, errorsappear in the printed specification requiring correction as follows:Page 1, line 68, after ca. insert 1 kg; page 2, line 63, for themisspelled word ben zonic read benzm'c; same page, line 93, followingthe formulae, insert the word respectively; and that the said LettersPatent should be read with these corrections therein that the same mayconform to the record of the case in the Patent Oflice.

Signed and sealed this 10th day of March, A. D. 1925.

[smn] KARL FENNING,

Acting Gommiesiomr of Patents.

